The Man That Got Away

by maxmosher

Late August, 2010. Rushing, I changed my shirt and my deodorant in the bathroom at work. After an eight-hour shift, I was meeting up with a guy from an internet dating site. We shall call him Scott. I had recently been broken up with in an email by the man who I ironically nicknamed the Gentleman. I was emotionally vulnerable, but wanted to get back in the game. No matter what I’ve been through with men, no matter how disastrous my heartbreaks, I’ve always been willing to try again.

I met Scott at Pauper’s Pub on Bloor Street. He was adorable, with curly red hair and a boyish smile. We talked about the Muppets, Joan Crawford and Canadian politics. Our first disagreement was about Michael Ignatieff.

“I actually like Ignatieff,” he claimed.

“Isn’t he just the worst example of a pompous, other-worldly academic who…”

“Okay. I lied. I agree with you.” He laughed.

“What a classic Liberal you are!”

It was the best first date of my life, made better when he agree to come back to my place. We cuddled in my bed and then began to kiss. Overjoyed, I blurted out, “I’m so relieved you’re kissing me!”

“Um,” he started. “What are you looking for right now?”

“What?” I asked, moving away from him. “What are you looking for right now?”

“Nothing serious. I’m still getting over my ex.”

It was like the bomb was going off slowly. In denial, I tried to curtail the unpreventable. “Okay. Scott, this is a first date. It’s going very well, and I want to have a second, but we just met.”

“I think I might have to leave it with one night.”


We lay in silence for some minutes.

“Scott, do you really think you’re going to meet another guy who wants to talk about the Muppets, Joan Crawford and Canadian politics?”

“Probably not…”

“Listen, it’s okay to go slow. I also have an ex who broke my heart. But you take it day by day…”

Then he began to cry.

He slept in the spare bedroom. The next day, he sent me an email which gave the excuse, “I think we both had too much to drink.” I never saw him again.


Late August, 2011. I rushed from work to meet Derrick. Having sworn off dating websites, I had met him on facebook when he ‘liked’ a status of mine. (My status updates are kind of a big deal.) I met him at Pauper’s Pub and he was even cuter than I expected. If you had written a list of features Max likes, you would check off every one: big dark eyes, check; scruffy beard, check; a face which would be intimidating in its handsomeness were its owner not so bashful, check! He had an easy going nature and an admirable community-building job to boot.

We talked about ‘Sesame Street’, Liza Minnelli and American politics. He stared intensely and a couple times openly mentioned that he was interested in me. I liked the Max I saw reflected in his eyes.

He offered to walk me home, and half way there (“Okay, Max, you do not live ‘right by’ Ossington Station!”) we both had to pee, which provided a good excuse to get him upstairs.

“I love your room!” he exclaimed, scanning the walls of all my Edward Gorey, Barack Obama and Vogue pictures. I fidgeted around, excusing the clutter, babbling on. I sat beside him on the bed to show him a book and was interrupted by him kissing me. It was nice kissing.

And this time I was determined to keep my mouth shut. Er, what I mean is, I was not going to say anything to provoke a scary “what do you want” conversation. We made out for ten minutes and he murmured my name softly. No one had ever done that before.

“Max,” he said, looking down on me with a smile, “Have I told you about the difficulty in dating me.”



“What is it!” I demanded, sitting straight up.

“I don’t do monogamy.”



“I just can’t close myself to experiences with anybody right now.”

“Right now…?”

“Or ever, I guess. Although I think I will find a special person to share my life with, I always want to be free to explore others sexually.”

“I see.”

“Are you all right?”

“Why is there always another shoe?” I asked the universe more than him.

“You’re not all right.”

One year after I met Scott, another ‘perfect’ man and I lay in silence. I could have thrown a hissy fit and kicked him out of my house. But what would I gain from that? I didn’t want a repeat of last summer. I didn’t want to lose him before getting to know him. How many guys out there want to discuss ‘Sesame Street’, Liza Minnelli and American politics?

“Maybe I shouldn’t have come,” Derrick said.

“Can you do me a favour?” I asked. “All my dating life people have made decisions without me. Can we just hold out on figuring this out?”

“Yes,” he answered. I kissed him. “I’m so glad you’re kissing me,” he said.

“I have one more question: do you think we might have something really special.”

“Yes, I do.”

“Okay, that’s all you need to say right now.”

It was dawn before we fell asleep.

The next day brought no more clarity. He rode with me on the subway as I went downtown for Jack Layton’s memorial. I told him I was going to my cottage for a week and a half.

“So I guess, if I’m lucky, I’ll see you in a week and a half…?”

He kissed me goodbye at the platform.

The getaway to Lake Simcoe was well timed: I didn’t take my lap top; I watched Indiana Jones movies and read P.G. Wodehouse and P.D. James (who I kind of thought were the same person until I bought paperbacks by both); I thought things over.

During day light, laying in the hammock or going for muddy walks, I’d think, ‘It’s not a big deal. Normally, You wouldn’t ask for exclusivity after a first date. He admitted you have something special and maybe he’ll adapt. He’s the best guy you’ve met in a really long time.’

At night, though, the demons of doubt would come: ‘Max, are you nuts? This guy was willing to jeopardize it on your first date? Non-monogamy is that important to him! What do you think is going to happen? He’s going to change for you, like the end of a romantic comedy? End it with him on facebook tomorrow!’

I should add that I support people’s right to have whatever kind of relationship they chose. The queer community has always pioneered different ways of loving and I admire that…in theory. But polyamory is not for me. I find it emotionally icky.

A drama-free open relationship, like visible abdominal muscles, is a myth of the gay community.

So I was left with a complex Catch 22. Start the conversation soon but risk ending it and always wondering what could have been, or give it time and wait for Derrick to fall in love so that he’d be open to compromise, but risk getting even more hurt.

I succumbed and borrowed my Mom’s laptop and snuck over to our neighbours’ log cabin to use their internet.

I had a message from Derrick: “Is it weird that I already miss you?”

“No weirder than me using my Mom’s laptop and our neighbours’ internet connection to check and see if you’d written me,” I typed.


Our second date went well. We rented ‘Burlesque’ and drank a lot of red wine. We managed to not bring up the pink elephant and, more surprising, I didn’t worry about it.

On our third date, I wasn’t so lucky. We were at an art event in Parkdale and Derrick started telling a supposedly funny story about going to “one of” his lover’s parties, an anniversary for him and his partner. Derrick, unknowing of whether the partner understood how close they were, got up to the open mic and told embarrassing stories about the lover. Afterwards, the partner gave him a hug of recognition.

Beyond becoming instantly jealous (Was this a current lover?) I asked myself if I actually wanted to be with someone who was so comfortable being the other man. I want to be part of a committed partnership, but not one in which our younger lovers come to our anniversary parties. With the seed planted in my mind, for the rest of the evening when he mentioned a boyfriend I couldn’t avoid thinking ‘Past or present?’

The next morning, I was so wracked with unease I almost made myself sick from worrying. Oblivious, he cuddled me.

Derrick and I didn’t talk for a week, but he continued to comment on everything I put on facebook. Perhaps I was postponing the conversation (which, despite my best efforts, I still thought of as an ultimatum) because I was hoping something would change.

One night in bed he had said to me, “Do you know how hard it is to meet nice, cute guys who are good conversationalists and good kissers?”

“Yes, I do.”

He surprised me by showing up at the Word on the Street festival. I was tired from being there all day at the WORN table and a little ill from too many sweet potato fries. My heart sunk when I realized I’d have to have the talk with him then.

“You look really hot today,” he said. My heart entered my stomach.

We went for a walk on the UofT campus. Although I could barely make eye contact with him, once I started, everything I had been worried about spilled out.

“I like you more than I’ve liked a guy in a long time. You’re incredible. I probably should have brought this up earlier, but I didn’t want to lose you before we had a chance to get to know each other. You were honest with me about monogamy on our first date, but I also let you know how I felt about your position. If I wasn’t more clear, it’s only because I liked you so much. If you had treated me less romantically, like a casual friend with benefits, maybe I wouldn’t be feeling this way. But I can’t fall in love with someone who wants to sleep with other people.”

We sat down on a grassy knoll in Philosopher’s Walk.

“Derrick, don’t make me ask the question you know I need to ask.”

“I like you a lot,” he finally sighed. “And I don’t treat anybody else the way I treat you. You are amazing and I think we have something special. But I can’t promise anybody monogamy.”

“Can’t promise monogamy?”

“You’re right, that’s bad wording. I don’t want monogamy.”

I told him the joke that had been brewing in my head for three weeks: “I can make you this deal: we can date other people after we break up.” He smiled weakly. I said, “Can I ask why?”

“I want to experience my friends and people I may meet in a lot of different ways, including sexually. I told you, I can’t close myself to good experiences.”

“Thing is, Derrick, you’re closing yourself to me right now. What about when you meet that special someone, you still want to be open?”

“Yeah. It’s something I’m always going to want.”

“Well,” I said. “I think that’s selfish. Being with someone, loving someone, sometimes means giving up stuff which would hurt them.”

He didn’t respond.

“Hasn’t this happen to you before?”

“Not really. I’ve had boyfriends, it’s just always ended over something else.”

“You’ve been lucky.”

“Yeah, I’ve been told that,” he said.

“This sucks,” I said.

“Can we at least be friends?”

I shook my head. “I don’t stay friends with exes. Most of my exes have hurt me too much.”

“You’re breaking up with me, Max.” I needed to hear the words come out of his mouth to actually believe it. “I’m going to really miss you. It makes me sad.”

“It makes me sad too.”

We got up and walked to the subway, mostly in silence. “Any extra time I can spend with you,” he said, wistfully. He stopped to pick up some smooth chestnuts and I almost started crying when he tried to give me one.

“Derrick, please, no…”

Outside the subway station he asked if he could invite me to his birthday party in December.

“No. I’m always going to wish I was your boyfriend.”

“Are you even going to delete me off facebook?”

“I don’t know. I’m going to go.” We hugged. It was tight and lengthy. “Listen, this sounds weird,” I whispered in his ear. “But I sort of love you.”

“Not weird at all,” he said, tears coming to his eyes.

“Please don’t message me. I’ll email you if I want to.”

“Okay,” he said.



I walked all the way home.


Postscript: That first evening, I grew angry that he hadn’t budged in his position. He didn’t waver about the non-monogamy in any way, wasn’t even tempted to try to stay with me. But soon I realized that this also showed that I did the right thing. We would have fought about it eventually and the break up would have been even harder.

I also realized that I was just as stubborn as him.

But the difference is that I’ve been a push over with guys in the past. The Max of four years ago might have stayed with him longer, or changed his mind mid-break up. The silver lining of this whole mini-romance is seeing plainly that I know who I am and can put myself first. Offered a relationship with a beautiful and wonderful guy, but one who would hurt me, I chose to be single.

And the freedom of choice is a wonderful thing.